[[Music/GeorgeJones This legendary country singer]] [[TearJerker has plenty of depressing songs]].
* "He Stopped Loving Her Today" is one of the saddest songs in country music, which is really saying something.
* "Choices" is sung from the perspective of a man who has ruined his life through alcohol addiction, and begins to realize this his predicament is his own doing. Simply put, it is a heartrending tearjerker of a song about how we all must live with the consequences of the decisions we make in life, a sentiment that seems especially credible coming from a reformed hellraiser like George.
* The narrator of "If Drinkin' Don't Kill Me (Her Memory Will)" is on the verge of drinking himself to death after realizing that he will never overcome the pain associated with his ex's memory.
* The narrator of "The Grand Tour" takes his listener on a tour of his house, only for the listener to suspect something is amiss and for the narrator to reveal the truth in the startling climax.
* "Who's Gonna Fill Their Shoes?" mourns the fact that the legends of country music are one-of-a-kind and irreplaceable.
** Even HarsherInHindsight now that the man himself is gone. Of all the artists mentioned in the song, only Music/JerryLeeLewis and Music/WillieNelson are still living (as of 2017).
* His duet with Tammy Wynette, "Golden Ring", is a devastating account of a man and woman from engagement to marriage to divorce. Jones and Wynette being freshly divorced themselves when they recorded it just adds more layers of sadness to the song.